Composition of matter



Patented Feb. 18, 1941 UNITED STATES PATENT OFFICE COMPOSITION OF MATTERNicholas Bennett, Widnes, England, assignor to Imperial ChemicalIndustries Limited, a corporation of Great Britain 9 Claims.

This invention relates to novel compositions of matter, and moreparticularly to compositions containing chlorinated rubber.

Many proposals have been made for preparing plastic and thermoplasticmasses containing chlorinated rubber by incorporating with it suchmaterials as vegetable oils, alkylated naphthalenes, and chlorinatedhydrocarbons such as chlorinated naphthalenes. In co-pending applicationSerial No. 153,675 filed July 14, 1937, I have described the preparationof compositions containing chlorinated rubber and the product obtainedby condensing-a chlorinated aromatic hydrocarbon with a chlorinatedaliphatic hydrocarbon.

This invention has as an object the manufacture of new and usefulcompositionsof matter.

Further objects reside in non-inflammable plastic masses comprisingchlorinated rubber compositions and methods for obtaining suchcompositions. Other objects will appear hereinafter.

I have now found that substantially non-inflammable compositions ofmatter can be obtained by incorporating with chlorinated rubber amaterial obtained by halogenating the product of a condensation betweenan aromatic hydrocarbon and a hydrocarbon containing a halogenatedaliphatic grouping. I find that by such a method, compositions areobtained which have a large proportion of halogen bound in a stablemanner, and exhibit a high resistance to flames.

Typical compounds having halogenated alivphatic groupings which may beused for the condensation, include methylene chloride, ethylenechloride, trichlorethylene, propyl chloride, chlorinated parafiin wax,and benzyl chloride, while suitable aromatic hydrocarbons with which tocondense such chlorinated compounds are benzene and its homologues ornaphthalene. Y

The condensation is suitably effected in known manner in the presence ofa catalyst consisting of an anhydrous metallicchloride such as aluminumchloride, or in the presence of boron halide or other catalysts used inthe Friedel-Crafts reaction. Thus the reactants are mixed and thecatalyst gradually added as evolution of gas proceeds. Alternatively,the catalyst may be mixed with one of the reactants, and the otherreactant then gradually added. Diluents may be added to facilitate thereaction, and heat may be applied during the whole or part of thecondensation. The crude condensation product may be halogenated, e. g.chlorinated either immediately or after a distillation or similarpurifica ticn step. The condensation product is usually a high boilingviscous liquid or a solid, and in order to facilitate the chlorinationit may be dispersed in a solvent such as carbon tetrachloride. Ahalogenv carrier, e. g. anhydrous ferric chloride,

may be added and chlorination carried out in the dark so that onlynuclear substitution. occurs. Alternatively the material may be heateduntil it is in a mobile condition, and chlorine then passed in. l

The final material may be incorporated withthe chlorinated rubberwithout any purification, or it may be distilled, extracted with asuitable solvent, or otherwise treated to puriiyit beforehand.

The incorporation of the chlorinatedcondensation product with thechlorinated rubber may be performed in any convenient manner, e. g. bymilling the two in a Werner-Pfleiderer mixer or a Baker-Perkins mixer,or one or both of the constituents may be dissolved in a common solventprior to mixing, and the solvent subsequently removed by evaporation.Fillers, pigments, and known plasticizers such as tricresyl phosphate ordibutyl phthalate may also be added.

The following examples illustrate the preparation of a typicalintermediate product and the preparation of the composition according tomy invention, all parts being by weight:

Example I Three hundred twelve (312') parts of benzene and parts ofanhydrous aluminum chloride were heated to 6070 C'., and 90 parts ofethylene dichloride were added. When evolution of hydrochloric acid hadceased, water was added and the mass agitated for an hour. It was thenneutralized with lime and distilled under reduced pressure. One part ofanhydrous ferric chloride was added to the distillate, which was thenchlorinated by heating it to C. and passing in 600 parts of chlorine.The product was then incorporated with an equal weight of chlorinatedrubber by dissolving each in toluene, mixing the two solutions andevaporating off the toluene.

Example II Six hundred fifty (650) parts of chlorinated paraffin wax(25.4% chlorine) were gradually added to a stirred mixture of 1056 partsof benzene and parts of aluminum chloride at 20 C. 50 After addition wascomplete, the mixture was heated to C. .for four hours, treated withwater and heated to 300 C. The oil thus obtained was filtered andchlorinated at C. in the presence of light to a chlorine content of17.2%. A 55 plastic composition containing chlorinated rubber and of theabove chlorinated condensation product was made by incorporating the twoconstituents in a Werner-Pfleiderer mixer.

The products of this invention are useful in the preparation of coatingcompositions of various types and. they may be used either with orwithout incorporated pigments, filler, etc. Such coating compositionsmay be applied to various types of rigid or semi-rigid surfaces asmetals of various kinds, wood, glass, rubber and rubberlike products,synthetic resin products, etc. The plastic masses may be used as suchfor producing molded products, for preparing insulating material, forluteing compounds, etc. In general the products may find applicationwherever chlorinated rubber compositions are useful but because of theirgreatly enhanced fire resistant properties they find extended use overthose uses.

to which the usual chlorinated rubber compositions are applied.

As many apparently widely different embodiments of this invention may bemade without departing from the spirit and scope thereof, it is to beunderstood that I do not limit myself to the specific embodimentsthereof except as de fined in the appended claims.

I claim:

1. A composition of matter comprising chlorinated rubber and the productobtained by halogenating the material obtained by reacting in thepresence of a Friedel-Crafts catalyst an aromatic hydrocarbon with ahydrocarbon having at least one halogen atom attached to an acycliccarbon atom.

2. The composition set forth in claim 1 in which said aromatichydrocarbon is benzene.

3. The composition set forth in claim 1 in which said aromatichydrocarbon is naphthalene.

4. The composition set forth in claim 1 in which said aromatichydrocarbon is benzene and said hydrocarbon containing a halogenatedaliphatic group is ethylene chloride.

5. The composition set forth in claim 1 in which said aromatichydrocarbon is benzene and said hydrocarbon containing a halogenatedalialiphatic group is chlorinated paraffin.

6. The composition set forth in claim 1 in which said aromatichydrocarbon is benzene and said hydrocarbon containing a halogenatedaliphatic group is benzyl chloride.

7. The composition set forth in claim 1 in which said aromatichydrocarbon is naphthalene and said hydrocarbon containing a halogenatedaliphatic group is ethylene chloride.

8. The composition set forth in claim 1 in which said aromatichydrocarbon is naphthalene and said hydrocarbon containing a halogenatedaliphatic group is chlorinated paraffin.

9. The composition set forth in claim 1 in which said aromatichydrocarbon is naphthalene and said hydrocarbon containing ahalogenating aliphatic group is benzyl chloride.

NICHOLAS BENNETT.

